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The Hotel Investor Playbook
Michael Russell & Nathan St Cyr
46 episodes
2 days ago
Most hotel investors default to syndication — raising capital from dozens of limited partners and layering in complex waterfalls. But what if there’s a smarter, simpler path? This week’s guest, Brandon Gore, is building The Outlier Hotel, a 10-cabin luxury retreat in Arkansas designed to last 100 years. Instead of chasing the traditional syndication model, he’s structuring the project as a joint venture — lowering pressure, creating strong cash flow, and unlocking tax advantages that limited ...
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Investing
Business
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All content for The Hotel Investor Playbook is the property of Michael Russell & Nathan St Cyr and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Most hotel investors default to syndication — raising capital from dozens of limited partners and layering in complex waterfalls. But what if there’s a smarter, simpler path? This week’s guest, Brandon Gore, is building The Outlier Hotel, a 10-cabin luxury retreat in Arkansas designed to last 100 years. Instead of chasing the traditional syndication model, he’s structuring the project as a joint venture — lowering pressure, creating strong cash flow, and unlocking tax advantages that limited ...
Show more...
Investing
Business
Episodes (20/46)
The Hotel Investor Playbook
The Beginner's Guide To Building Wealth In Hospitality | Jonathan Mueller E43
Think you need a perfect plan to start investing in hospitality? Think again. In this episode, we sit down with Jonathan Mueller, an everyday investor who went from zero experience and a failed multifamily deal to buying a $250K roadside motel and building a growing hospitality portfolio. He didn’t have a background in hotels, didn’t have much of a strategy, and still made it work through pure action, problem-solving, and a willingness to pivot. You’ll learn: Why taking action beats waiting f...
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1 week ago
43 minutes

The Hotel Investor Playbook
Hotel Marketing Decoded: What Every Owner Needs to Know | Anthony Chiaravallo E42
Is your marketing helping your hotel or just draining your budget? In this episode, we sit down with Anthony Chiaravallo, founder of Vallo Media, who has managed over $100M in ad spend for brands like Nike, Resorts World, and boutique hotels across the country. Whether you're trying to fill beds or scale a brand, Anthony breaks down how to think about hotel marketing in a way that actually drives bookings. You’ll learn: How to build a full-funnel strategy that drives real bookingsWhat makes a...
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2 weeks ago
44 minutes

The Hotel Investor Playbook
Syndication Simplified: The Strategy That Builds Generational Wealth | Desiree Doubrox E41
Ever wondered how people raise millions to buy real estate without using their own money? In this episode, Desiree Doubrox breaks down the world of syndication and how she built an eight-figure fund while empowering hundreds of others to do the same. Whether you're new to investing or ready to raise capital for your first deal, this conversation simplifies the path to building generational wealth. You’ll learn: What syndication really is and how it applies beyond real estateHow to gain credib...
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3 weeks ago
52 minutes

The Hotel Investor Playbook
A Masterclass In Experiential Hospitality With The Bolt Farm Treehouse Founders | Tori and Seth Bolt E40
Instead of chasing bookings, the founders behind Bolt Farm Treehouse create an obsession amongst their guests, and they do it with love at the center of everything. Their hospitality business heals relationships, attracts top-tier employees, and doesn't require the use of OTAs In this episode, Seth and Tori Bolt break their iconic hospitality business where luxury stays meet emotional transformation. You’ll hear: How to design experiences that emotionally move your guestsWhy 100% of their boo...
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4 weeks ago
54 minutes

The Hotel Investor Playbook
$187M Hotel Portfolio by Age 30: How to Choose the Right Deals, Brands, and Ops Model | Sujay Mehta E39
Thinking about buying or operating a hotel, but not sure where to start? Sujay Mehta built a $187M hospitality portfolio by betting on himself, starting lean, and learning through execution. In this episode, he breaks down what most people get wrong about hotel investing and how you can start smarter. You’ll learn: How to determine which hotel brand fits a deal bestHow the “Mamba Mentality” shaped his risk tolerance and executionWhat he learned by making his first deal a ground-up development...
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1 month ago
1 hour 10 minutes

The Hotel Investor Playbook
Turning Passion into Profit in Rural Hospitality | Dave Cook E38
What does it take to build a successful hospitality business in a small rural town, with no outside investors? Dave Cook, founder of Barn Door Hostel in Rumney, New Hampshire, walks us through his journey from hostel volunteer to hostel owner. We dive into: How he used sweat equity and personal savings to convert an old chicken coop into a thriving hostelHis research process on demand, shared economy trends, and local recreation patternsThe hidden cost of rural hospitality: zoning, septic, AD...
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1 month ago
44 minutes

The Hotel Investor Playbook
Bootstrapped Hospitality: Scaling Your Hotel Portfolio Without Major Capital | Austin Phippen E37
Today’s guest bought a roadside motel in a town of 900 people and turned it into a thriving hospitality brand. In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Austin Phippen, a 26‑year‑old owner of Chama Trails Motel, a portfolio of 12 short-term rentals and a scenic wedding venue in Chama, New Mexico. What you’ll learn from this episode: The “Motel Hack” mindset: How Austin got in with seller financing and turned the motel into both home and businessScaling withou...
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1 month ago
37 minutes

The Hotel Investor Playbook
Building a Scalable Outdoor Hospitality Brand Through Franchising | Brian Linton E36
In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Brian Linton, co-founder of Finding Promised Land, Camp Ferncrest, and The Rex Hotel. Brian shares how he transitioned from building a $20M apparel company to launching one of the fastest-growing outdoor hospitality brands in the U.S. Key Topics: How a rundown motel purchase during COVID led to a hospitality empireNavigating zoning issues, STR restrictions, and neighborhood pushbackWhat to look for in land: acreage, u...
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1 month ago
1 hour

The Hotel Investor Playbook
How to Know If Your CPA Is Helping You or Holding You Back | Kelly Tate E35
Not sure if your tax advisor is actually optimizing your returns, or just filing forms? In this episode of the Hotel Investor Playbook, we’re joined by Kelly Tate, a CPA with over two decades of experience helping real estate and hospitality investors navigate the tax code with confidence. We dive into key strategies like bonus depreciation, Section 179, and cost segregation, and explore how to structure your entities to maximize tax efficiency, especially when you’re juggling both real estat...
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2 months ago
51 minutes

The Hotel Investor Playbook
Why Hostels Are an Untapped Investment Opportunity in the U.S. | Mike & Nate E34
We're proving why hostels are one of the most powerful investment models in real estate. In this episode, Mike and Nate break down exactly why they’re going all-in on hostels and how they turn underperforming assets into award-winning hospitality destinations. You’ll learn: Why the U.S. hostel market is ripe for disruptionThe revenue model that turns $100 rooms into $300 cash machinesHow their guest-first brand became a marketing engineWhy “flawed” properties are actually a goldmine for this ...
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2 months ago
36 minutes

The Hotel Investor Playbook
The Strategic Power of Third-Party Hotel Management | Bryan Fish E33
You don’t need to be an expert in everything to scale in hospitality, just need to align with the right consultants, operators, and partners who’ve done it before. In this episode, we sit down with Brian Fish, CEO of Reliance Hospitality, to unpack how third-party operators help investors go from scrappy operators to institutional-level players. Brian shares what most owners get wrong during acquisitions, how franchise agreements really work behind the scenes, and why your ability to scale co...
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2 months ago
45 minutes

The Hotel Investor Playbook
He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32
After helping scale a family office real estate portfolio from $3 million to over $320 million, Reilly Brennan walked away from the comfort of a W-2 job to carve his own path in boutique hospitality. In this episode, we sit down with Reilly to unpack how he sourced and acquired two independent hotels in Duluth, Minnesota, one through creative seller financing, the other straight off LoopNet. We break down his underwriting process, deal structure, construction strategy, and how he’s building ...
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2 months ago
46 minutes

The Hotel Investor Playbook
Building a $6M Micro Resort with Only 3% Down Using a USDA Loan | Ian Joseph E31
In this episode, we dive into an uncommon but powerful financing strategy that could change how boutique hospitality projects get funded. Ian Joseph, founder of Branch, shares how he’s leveraging a USDA Rural Business Development loan to finance a $6M micro resort buildout in West Virginia - with just 3% down. We break down the entire capital stack, how USDA loans work for ground-up hospitality development, and why this financing tool is often overlooked by small to mid-size investors. Ian al...
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3 months ago
47 minutes

The Hotel Investor Playbook
The Ultimate Guide To Financing Your Next Hotel Deal | Suraj Desai E30
In this episode of the Hotel Investor Playbook, we sit down with Suraj Desai, a hospitality finance expert who has helped close hundreds of hotel deals, to unpack everything you need to know about financing your next acquisition, renovation, or ground-up development. Suraj breaks down the full capital stack, from SBA 7a and 504 loans to bridge, CMBS, and mezzanine debt. He explains which types of financing work best for boutique hotels vs. flagged assets, why banks are pulling back, and what ...
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3 months ago
53 minutes

The Hotel Investor Playbook
Buying Hotels Is Just the Start: How to Build a Lasting Hospitality Brand | Keir Weimer E29
In this episode of the Hotel Investor Playbook, we sit down with Keir Weimer, founder of Weekender Hotels, to unpack how he’s building a boutique hospitality brand designed for the long haul. Keir shares how he aligned his business with his personal lifestyle, his on-the-road strategy for sourcing deals, and the frameworks he’s using to scale Weekender into a generational hospitality company. We dive into why building a recognizable brand creates enterprise value beyond just owning hotel asse...
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3 months ago
48 minutes

The Hotel Investor Playbook
Hotel Investing Insights from the CEO of One of America’s Top Hotel Brokerage Firms | Suraj Bhakta E28
What does it really take to scale from your first hotel acquisition to managing a hospitality portfolio worth tens or even hundreds of millions? In this episode, Michael and Nate sit down with Suraj Bhakta, CEO of NewGen Advisory, a leading hospitality brokerage with offices across 12 states and transactions in 44. Suraj brings over two decades of commercial real estate experience, having closed $850 million in hotel deals and facilitated nearly $500 million in capital raises. He’s also Chief...
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3 months ago
52 minutes

The Hotel Investor Playbook
Saturday Special: Behind the Curtain at Malama Capital | Mike & Nate E27
In this special Saturday edition, we’re flipping the script. No guest today — just Mike and Nate giving you a behind-the-scenes look at what’s going on inside Malama Capital. After a listener reached out asking to hear more about our journey, we decided to hit record and share where we’re at, what we’re focused on, and how we’re thinking about the road ahead. We cover: Why Q2 is all about acquisitions and our $10M purchase goal How we’ve restructured our team to create more bandwidth Usin...
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3 months ago
25 minutes

The Hotel Investor Playbook
How Sky McLean Built a $500M Hotel Brand from Scratch | Sky McLean E26
What do you do when you get fired from your job and get escorted out with a cardboard box? If you’re Sky McLean, you build one of the fastest-growing hospitality brands in Canada. In this episode, we sit down with Sky McLean, founder and CEO of Basecamp Resorts, owner of 14+ resorts, and operator of over half a billion in real estate. From bootstrapping her first hotel with a BMW loan to raising $40 million through Instagram, Sky’s story is a masterclass in grit, creativity, and bold vision. ...
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3 months ago
38 minutes

The Hotel Investor Playbook
Glamping for Profit: Low Cost, High Cash Flow, Massive Upside | Zac Willms E25
What if you could double your money in one season with glamping tents? Zac Willms is pulling it off — and building a profitable outdoor brand in the process. In this episode, Mike and Nate talk with Zac Willms, co-owner of a thriving glamping resort in Tobermory, Ontario. Zac shares how he turned a neglected trailer park into a profitable outdoor hospitality destination, the simple formula behind his success, and why buying an old campground might be the real cheat code. We unpack everything ...
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4 months ago
51 minutes

The Hotel Investor Playbook
Olympic Discipline, Million-Dollar Loss, and Building a Hospitality Portfolio | Adam G Dailey E24
From Olympic Trials to Losing Millions—And Bouncing Back With a Boutique Hotel Empire In this episode of Hotel Investor Playbook, Mike and Nate are joined by Adam Dailey, a former 5x All-American athlete turned hospitality investor. Adam shares his wild journey—from building a multimillion-dollar business, losing it all in a matter of weeks, to bouncing back stronger with a growing portfolio of boutique hotels, hostels, and STRs. We unpack: •How championship-level discipline translates to hig...
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4 months ago
1 hour 7 minutes

The Hotel Investor Playbook
Most hotel investors default to syndication — raising capital from dozens of limited partners and layering in complex waterfalls. But what if there’s a smarter, simpler path? This week’s guest, Brandon Gore, is building The Outlier Hotel, a 10-cabin luxury retreat in Arkansas designed to last 100 years. Instead of chasing the traditional syndication model, he’s structuring the project as a joint venture — lowering pressure, creating strong cash flow, and unlocking tax advantages that limited ...